Montgomery Homes with Attached Parking features

Welcome to Montgomery, New York – a charming village nestled in the heart of Orange County, where history meets modern living. With its picturesque landscapes and close-knit community, Montgomery offers a unique blend of small-town charm and convenient access to urban amenities. Just a short drive from the bustling city of Newburgh and the scenic Hudson River, residents enjoy the best of both worlds – tranquil living with the vibrancy of city life nearby.

Montgomery is steeped in rich history, evident in its well-preserved architecture and friendly atmosphere. The village is known for its beautiful parks, local shops, and community events that bring neighbors together. Outdoor enthusiasts will love the nearby hiking trails and recreational opportunities, making it a perfect place for families and individuals alike.

When it comes to housing, Montgomery boasts an array of homes that cater to diverse lifestyles. One of the standout features of many properties in this area is the availability of attached parking. Say goodbye to the hassle of street parking and embrace the convenience of having your own dedicated space right at home. Whether you’re a busy professional or a growing family, this feature adds an extra layer of comfort and practicality to your living experience.

Explore the charm of Montgomery, where you can find homes that not only reflect your style but also accommodate your needs with the convenience of attached parking. Discover your dream home in this delightful village, where community spirit and modern convenience come together seamlessly!

Newest Montgomery Homes with Attached Parking features

$510,000

4 Beds ⋅ 3 Baths ⋅ 1032471 MLS

Welcome to this beautiful, meticulously maintained, thoughtfully upgraded, 4 bedroom, 3 full bath, built just three years ago! From your first step inside, you'll notice how gorgeous this home is as the amenities shine through. Open floor plan shows off the large living room, formal dining room, eat-in kitchen with center island, stainless steel appliances, granite countertops, custom tile backsplash, and an abundance of cabinets. 13ft vaulted ceilings highlight how the home fills with natural light. Step out onto the upper deck for great views and bbq. Spacious master bedroom with en suite, double vanity, and walk-in closet. Laundry room on the main floor. Additionally, we have the fourth bedroom, additional full bathroom, and family room on the lower level - great for a separate suite, guests, extended family, or just bonus recreation room. Check out to the private lower level deck. Town water & sewer, natural gas connected, great location, and amazing neighborhood. Valley Central Schools. Ready to move right in!

9 Overlook Terrace, Montgomery

$669,000

4 Beds ⋅ 3 Baths ⋅ 1026839 MLS

One incredibly upgraded home with two driveways and two garages! This fully renovated 4-bedroom, 2.5-bath, 2,646-square-foot Colonial checks boxes you didn't even know you had. A second driveway leads to a heated 24x30 workshop with a car lift, ideal for hobbyists or anyone needing serious workspace, plus a portable garage for extra storage. Inside, hardwood floors run throughout the freshly painted main level, complemented by crown molding, solid wood doors, custom built-ins, and two fireplaces. The updated kitchen features quartz counters, a marble island, and stainless steel appliances. New Andersen sliders open to a covered Trex deck with overhead fans and lighting — a true all-weather entertaining space. The finished basement (not included in square footage) adds bonus living space perfect for a game room, media room, or home gym. Upstairs, the primary suite offers an updated ensuite bath and a custom California closet with pocket door. Major systems have been thoughtfully updated: new roof (2024), high-efficiency Ascent furnace (2024), Roth oil tank (2025), expansion tank (2026), car lift (2025), Andersen sliders (2023), and carpet (2024). Kitchen, bathrooms, and lighting have all been refreshed within the last two years. Set on 1.7 private acres with fruit trees — and the pool table and hot tub are included. Move-in ready with nothing left to do but enjoy it.

83 Little Collabar Road, Montgomery

$724,000

4 Beds ⋅ 3 Baths ⋅ 1018110 MLS

Private 6.5-acre Victorian retreat with heated salt water pool! Tucked away on a quiet cul-de-sac, this impressive home features a dramatic two-story foyer, soaring ceilings, creates a grand first impression and leads to spacious living areas throughout the home and a flexible floor plan with exceptional potential on each floor including the walk out basement. Enjoy scenic views, generous indoor and outdoor living, and a prime location just minutes from shopping, dining, and Woodbury Common Premium Outlets. The main level features a generously sized formal dining room, ideal for entertaining, holiday gatherings, and everyday living. A private den or home office provides the perfect space for remote work, studying, or a quiet retreat. One of the home’s standout features is the expansive bonus room, larger than the primary suite and complete with its own private entrance. This versatile space offers endless possibilities, whether used for multigenerational living, guest accommodations, a second home office, a media or game room, fitness studio, or creative workspace. The spacious eat-in kitchen provides ample room for casual dining and opens directly to a deck overlooking the above ground pool and the breathtaking natural surroundings. Enjoy peaceful mornings, outdoor dining, and unforgettable sunsets while taking in the beauty and privacy of approximately 6.5 acres. The expansive property also offers room for future enhancements or expansion. A conveniently located first-floor laundry room with a utility sink adds everyday practicality and convenience. The spacious primary suite serves as a private retreat, showcasing a distinctive octagonal tray ceiling, an en-suite bathroom, and an oversized walk-in closet with abundant storage. The walk-out basement expands the home’s possibilities by providing direct access to the outdoor patio, creating a seamless connection between indoor and outdoor living while offering additional space for recreation, entertaining, or future finishing. The shed presents an exciting opportunity to create a charming pool cabana, hobby space or workshop. Additional highlights include above-ground oil heating and an attached two-car garage. Whether you’re searching for privacy, versatility, scenic surroundings, or room to grow, this exceptional Victorian estate offers a rare opportunity to create the lifestyle you’ve been dreaming of. Make an appointment for a private tour and experience this beauty for yourself!

27 Grosso Court, Montgomery

$449,000

3 Beds ⋅ 1 Baths ⋅ 1018676 MLS

AVAILABLE! Welcome to this beautifully renovated 3-bedroom ranch set on a private 1-acre lot in Hamptonburgh, directly across from Thomas Bull Memorial Park. recently renovated and move-in ready, this home features refinished hardwood flooring, a bright updated kitchen with casual dining area, 1 full bath, new roof, new siding, and a charming new front porch. new driveway, new ductless air conditioning and heating units, freshly painted. The covered rear deck is perfect for relaxing, entertaining, or simply enjoying the peaceful surroundings. A large detached 2-car garage with water and electric provides excellent space for parking, storage, hobbies, or a workshop. With its fresh updates, inviting layout, and scenic location near parks, recreation, and commuter conveniences, this home is a wonderful Hudson Valley find.

230 Route 416, Montgomery

$769,900

3 Beds ⋅ 3 Baths ⋅ 977565 MLS

Thoughtfully designed, expertly built, and meticulously maintained, this 2003 Stunning Custom built Colonial by Hillside Homes is set on a private 2.2 acre wooded lot on a cul-de-sac in the Winding Oaks Subdivision. With 3400 square feet of modern luxury, this home features a large primary ensuite, two additional bedrooms, a bonus guestroom/study, an upstairs laundry room, and 2.5 bathrooms. The kitchen was fully remodeled in 2022 with modern cabinetry, quartz counter tops and a dual gas top with electric range. Nine-foot ceilings on the main level accentuate a magnificent fireplace in the family room and large upgraded windows, while oak flooring, arched doorways and pocket doors for privacy add elegance throughout the home. A spacious two-car garage includes a modern EV charger, and the side entrance to the home opens to a great built-in mudroom bench and closet for convenience. Downstairs, a walk-out basement offers a splendid recreation room with built-in bookshelves, a spacious office, and a large storage and utility room. The beautifully landscaped property features a well-maintained pool and a large stamped concrete patio making this home great for entertaining. It also features a 12 x 16 custom built shed and a practical fenced-in vegetable garden. Close to schools and shopping with convenient access to Metro North, this elegant home perfectly blends privacy, comfort and convenience, ideal for embracing the peaceful Hudson Valley Lifestyle.

42 Philip Drive, Montgomery

$874,999

3 Beds ⋅ 2 Baths ⋅ 982897 MLS

TOWN OF CRAWFORD LOG HOME SITUATED ON 25+ ACRES OF SERENE WOODED LAND. This charming 3-bedroom, 2-bathroom log home is situated in the Town of Crawford, within the Pine Bush School District. Conveniently located just 10-15 minutes from local restaurants, shopping centers, and essential services such as banking and postal facilities, this home offers both comfort and accessibility. Surrounded by nature, it is near several parks, including the Crawford Walking Trail and Winding Hills County Park. Major highways, including Route 17K, Route 302, and Interstate 84, provide easy access to Orange County Airport and Stewart International Airport, making travel and commuting effortless. The location is just the start check out the amenities this home has to offer starting with the kitchen combining classic craftsmanship with contemporary convenience. Deep green cabinetry with black iron hardware is complemented by butcher block style countertops, offering both style and function. A farmhouse sink sits beneath a row of large windows, allowing natural light to fill the space while providing a view of the surrounding trees. Exposed log beams and wood-paneled ceilings add to the warm, rustic aesthetic, while stainless steel appliances integrate modern practicality. The open-concept living and dining areas highlight the home’s impressive architecture. Vaulted ceilings with exposed log rafters create an airy, spacious feel, while large windows frame the natural scenery. The dining space sits beneath a classic chandelier, while the adjacent living area is anchored by a floor-to-ceiling stone fireplace, complete with a wood-burning stove. The natural wood flooring enhances the seamless flow between spaces, emphasizing the home’s log cabin character. The main level bathroom features a modern-rustic blend of design elements, including a sleek vanity with matte black fixtures, a bold patterned tile floor, and a tiled shower with classic subway tile detailing. Upstairs, the lofted ceilings continue into the bedrooms, where exposed log beams create a distinctive, cozy atmosphere. Large windows allow for ample natural light, while the combination of wood and neutral-toned walls maintains a balanced aesthetic. Plush carpeting provides warmth underfoot, and built-in storage adds functionality to the space. The second bathroom reflects a refined yet rustic style, featuring a modern black vanity, a crisp white sink, and a walk-in shower with elegant marble-patterned tile. The contrast between the wood ceiling and the contemporary finishes gives the space a refined yet cohesive look. The property extends to an expansive backyard, bordered by mature trees for privacy and natural beauty. A secondary outbuilding offers additional storage, workspace options or an additional two car garage. The peaceful setting, combined with the home’s well-crafted details and thoughtful updates, makes this property a timeless retreat. This will not last long on the market, don't delay, call now for your showing!!!

294 Comfort Trail, Montgomery

$1,145,000

4 Beds ⋅ 3 Baths ⋅ 975612 MLS

Your private retreat in the Hudson Valley, 80 minutes from the city. Ten estate-like acres, a heated pool, and total seclusion. With Stewart Airport just 30 minutes out and the best of the region within easy reach: golf, fishing, boating, lakes and rivers, miles of hiking, skiing, and the charming hamlets of the Valley, with the Shawangunk Ridge and the Catskills close by. The home lives up to the land. Renovated and move-in ready, it's an easy place to land — a bright, open layout, hardwood floors throughout, a chef's kitchen designed for gatherings and entertainment with a built-in wine fridge, and a primary suite that's its own escape, with a spa bath and soaking tub. Generous rooms flex to whatever you need — guests, media room, home gym, office. The massive basement is a blank canvas for any passion: wine cellar, fitness room, home theater, or all three. Major systems are done — bathrooms, floors, kitchen, pool, and deck renovated, plus new HVAC, water heater, and a meticulously maintained water-treatment system. Nothing to do but settle in. Outside, the grounds are made for it — a massive deck with built-in Sonos sound, a freshly redone 20x40 heated pool for long summer days, a fire pit for starry evenings, an enclosed garden with grapevines, a private orchard, a playground, and a pad with water and shore power for a camper, boat, or trailer. Woods and open space, entirely your own. Space, privacy, and the city never far. Come see it for yourself.

170 Dickerson Avenue, Montgomery

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